1,4-Naphthalenedione
- Formula: C10H6O2
- Molecular weight: 158.1534
- IUPAC Standard InChI: InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H
- IUPAC Standard InChIKey: FRASJONUBLZVQX-UHFFFAOYSA-N
- CAS Registry Number: 130-15-4
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: 1,4-Naphthoquinone; α-Naphthoquinone; p-Naphthoquinone; 1,4-Dihydro-1,4-diketonaphthalene; 1,4-Naphthylquinone; 1,4-Naphthaquinone; USAF CY-10; 1,4-Naftochinon; Rcra waste number U166; NSC 9583; Naphthoquinone
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Gas phase thermochemistry data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -23.3 ± 0.45 | kcal/mol | Ccb | Ribeiro Da Silva, Ribeiro Da Silva, et al., 1989 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 14.99 | 100. | Singh S.N., 1969 | Comparison with values estimated by difference method [ Dorofeeva O.V., 1997] supposes that selected value of S(298.15 K) can be underestimated by 20 J/mol*K. Uncertainty of Cp(298.15 K) is evaluated as 10 J/mol*K.; GT |
| 24.097 | 200. | ||
| 35.500 | 298.15 | ||
| 35.903 | 300. | ||
| 46.967 | 400. | ||
| 56.472 | 500. | ||
| 64.175 | 600. | ||
| 71.960 | 700. | ||
| 75.339 | 800. | ||
| 79.412 | 900. | ||
| 82.691 | 1000. | ||
| 85.523 | 1100. | ||
| 87.636 | 1200. | ||
| 89.847 | 1300. | ||
| 91.511 | 1400. | ||
| 92.921 | 1500. |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 9.5 ± 0.1 | eV | N/A | N/A | L |
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 1.81 ± 0.11 | TDEq | Chowdhury, Heinis, et al., 1986 | ΔGea(423 K) = 40.2 kcal/mol; ΔSea = -4.0 eu; B |
| 1.804 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -40.2 kcal/mol; ΔSea =-4.0, est. from data in Heinis, Chowdhury, et al., 1988; B |
| >0.799982 | ECD | Chen and Wentworth, 1983 | B |
| >0.598425 | ES | Collins, Christophorou, et al., 1970 | B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.4 | PE | Millefiori, Gulino, et al., 1990 | LL |
| 9.67 ± 0.02 | PE | Redchenko, Freimanis, et al., 1980 | LLK |
| 9.49 | PE | Lauer, Schafer, et al., 1975 | LLK |
| 9.56 ± 0.01 | PI | Potapov and Sorokin, 1971 | LLK |
| 9.60 | PE | Millefiori, Gulino, et al., 1990 | Vertical value; LL |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C6H4+ | 15.7 ± 0.2 | ? | EI | Grutzmacher and Lohmann, 1967 | RDSH |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | SE-30 | 180. | 1410. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS; Column length: 2. m |
| Packed | SE-30 | 190. | 1418. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS; Column length: 2. m |
| Packed | SE-30 | 200. | 1427. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS; Column length: 2. m |
Kovats' RI, polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | Carbowax 20M | 180. | 2205. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS (60-80 mesh); Column length: 2. m |
| Packed | Carbowax 20M | 190. | 2216. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS (60-80 mesh); Column length: 2. m |
| Packed | Carbowax 20M | 200. | 2228. | Llobera and García-Raso, 1987 | N2, Chromosorb P AW DMCS (60-80 mesh); Column length: 2. m |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Methyl Silicone | 1365. | Oda, Yasuhara, et al., 1998 | 25. m/0.25 mm/0.25 μm, He; Program: 50 0C (2 min) 20 0C/min -> 160 0C 5 0C/min -> 210 0C 10 0C/min -> 300 0C |
Lee's RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5MS | 241.61 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 10. K/min; Tend: 310. C |
| Capillary | DB-5MS | 241.61 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 4. K/min; Tend: 310. C |
| Capillary | SPB-5 | 241.6 | Knobloch and Engewald, 1993 | 40. C @ 2. min, 4. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tend: 300. C |
| Capillary | SE-52 | 240.82 | Boenke and Ballschmiter, 1987 | Hydrogen, 3. K/min; Column length: 12. m; Tstart: 120. C; Tend: 285. C |
| Capillary | SE-52 | 240.82 | Lee, Vassilaros, et al., 1979 | 12. m/0.3 mm/0.34 μm, He, 2. K/min; Tstart: 50. C; Tend: 250. C |
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Ribeiro Da Silva, Ribeiro Da Silva, et al., 1989
Ribeiro Da Silva, M.A.V.; Ribeiro Da Silva, D.M.C.; Teixeira, J.A.S.,
Enthalpies of combustion of 1,4-naphthoquinone, 9,10-anthraquinone, 9,10-phenanthraquinone, 1,4,9,10-anthradiquinone, 5,8-dihydroxy-1,4-naphthoquinone, and 1,4-dihydroxy-9,10-anthraquinone,
J. Chem. Thermodyn., 1989, 21, 265-274. [all data]
Singh S.N., 1969
Singh S.N.,
Thermodynamic properties of some condensed ring quinones,
Indian J. Pure Appl. Phys., 1969, 7, 52-53. [all data]
Dorofeeva O.V., 1997
Dorofeeva O.V.,
Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]
Chowdhury, Heinis, et al., 1986
Chowdhury, S.; Heinis, T.; Grimsrud, E.P.; Kebarle, P.,
Entropy Changes and Electron Affinities from Gas-Phase Electron Transfer Equilibria: A- + B = A + B-,
J. Phys. Chem., 1986, 90, 12, 2747, https://doi.org/10.1021/j100403a037
. [all data]
Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr.,
Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN],
J. Am. Chem. Soc., 1985, 107, 2291. [all data]
Heinis, Chowdhury, et al., 1988
Heinis, T.; Chowdhury, S.; Scott, S.L.; Kebarle, P.,
Electron Affinities of Benzo-, Naphtho-, and Anthraquinones Determined from Gas-Phase Equilibria Measurements,
J. Am. Chem. Soc., 1988, 110, 2, 400, https://doi.org/10.1021/ja00210a015
. [all data]
Chen and Wentworth, 1983
Chen, E.C.M.; Wentworth, W.E.,
Determination of molecular electron affinities using the electron capture detector in the pulse sampling mode at steady state,
J. Phys. Chem., 1983, 87, 45. [all data]
Collins, Christophorou, et al., 1970
Collins, P.M.; Christophorou, L.G.; Chaney, E.L.; Carter, J.G.,
Energy Dependence of the Electron Attachment Cross Section and the Transient Negative Ion Lifetime for p-Benzoquinone and 1,4-naphthoquinone,
Chem. Phys. Lett., 1970, 4, 10, 646, https://doi.org/10.1016/0009-2614(70)80108-7
. [all data]
Millefiori, Gulino, et al., 1990
Millefiori, S.; Gulino, A.; Casarin, M.,
UV Photoelectron spectra, reduction potentials and MO calculations of intramolecularly hydrogen-bonded naphtoquinones,
J. Chim. Phys., 1990, 87, 317. [all data]
Redchenko, Freimanis, et al., 1980
Redchenko, V.V.; Freimanis, Y.F.; Dregeris, Y.Y.,
Photoelectron Spectroscopy of 2,3-Disubtituted naphthoquinones,
J. Gen. Chem. USSR, 1980, 50, 1507, In original 1847. [all data]
Lauer, Schafer, et al., 1975
Lauer, G.; Schafer, W.; Schweig, A.,
Assignment of the four lowest ionized states of p-benzoquinone and the question of "lone pair" splitting in this system,
Chem. Phys. Lett., 1975, 33, 312. [all data]
Potapov and Sorokin, 1971
Potapov, V.K.; Sorokin, V.V.,
Photoionization and ion-molecule reactions in quinones and alcohols,
High Energy Chem., 1971, 5, 435, In original 487. [all data]
Grutzmacher and Lohmann, 1967
Grutzmacher, H.-F.; Lohmann, J.,
Massenspektrometrie instabiler organischer Molekule. I. Ionisations-potential und Bildungsenthalpie von Dehydrobenzol,
Ann. Chem., 1967, 705, 81. [all data]
Llobera and García-Raso, 1987
Llobera, A.; García-Raso, A.,
Gas chromatographic behaviour of several p-quinones,
J. Chromatogr., 1987, 393, 2, 305-311, https://doi.org/10.1016/S0021-9673(01)94227-X
. [all data]
Oda, Yasuhara, et al., 1998
Oda, J.; Yasuhara, A.; Matsunaga, K.; Saito, Y.,
Identification of polycyclic aromatic hydrocarbons of the particulate accumulated in the tunnel duct of freeway and generation of their oxygenated derivatives,
Jpn. J. Toxicol. Environ. Health, 1998, 44, 5, 334-351, https://doi.org/10.1248/jhs1956.44.334
. [all data]
Chen, Keeran, et al., 2002
Chen, P.H.; Keeran, W.S.; Van Ausdale, W.A.; Schindler, D.R.; Roberts, D.W.,
Application of Lee retention indices to the confirmation of tentatively identified compounds from GC/MS analysis of environmental samples, Technical paper, Analytical Services Division, Environmental ScienceEngineering, Inc, PO Box 1703, Gainesville, FL 32602, 2002, 11. [all data]
Knobloch and Engewald, 1993
Knobloch, T.; Engewald, W.,
Identification of some polar polycyclic compounds in emissions from brown-coal-fired residential stoves,
J. Hi. Res. Chromatogr., 1993, 16, 4, 239-242, https://doi.org/10.1002/jhrc.1240160407
. [all data]
Boenke and Ballschmiter, 1987
Boenke, A.; Ballschmiter, K.,
Fused quinones as retention index marker in high resolution gas chromatography with electron-capture detection (HRGC/ECD) of oxidized aromatic compounds,
Fresenius J. Anal. Chem., 1987, 327, 1, 44-45, https://doi.org/10.1007/BF00474554
. [all data]
Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M.,
Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons,
Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas EA Electron affinity IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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